Organic alloy for organic optoelectronic device, organic optoelectronic device, and display device

ABSTRACT

Disclosed are an organic alloy for an organic optoelectric device that is an organic alloy of at least two kinds of organic compounds, the at least two kinds of organic compounds includes a first organic compound and a second organic compound, a difference between evaporation temperatures of the first organic compound and the second organic compound is less than or equal to about 20° C. at less than or equal to about 10 −3  torr, and a light emitting wavelength of the organic alloy is different from light emitting wavelengths of the first organic compound, the second organic compound, and a simple mixture of the first organic compound and the second organic compound, and an organic optoelectric device and a display device including the organic alloy.

TECHNICAL FIELD

An organic alloy for an organic optoelectric device, an organicoptoelectric device, and a display device are disclosed.

BACKGROUND ART

An organic optoelectric device is a device that converts electricalenergy into photoenergy, and vice versa.

An organic optoelectric device may be classified as follows inaccordance with its driving principles. One is a photoelectric devicewhere excitons generated by photoenergy are separated into electrons andholes and the electrons and holes are transferred to differentelectrodes respectively and electrical energy is generated, and theother is a light emitting device to generate photoenergy from electricalenergy by supplying a voltage or a current to electrodes.

Examples of the organic optoelectric device include an organicphotoelectric device, an organic light emitting diode, an organic solarcell, and an organic photo-conductor drum, and the like.

Among them, the organic light emitting diode (OLED) has recently drawnattention due to an increase in demand for flat panel displays. Theorganic light emitting diode converts electrical energy into light byapplying current to an organic light emitting material, and has astructure in which an organic layer is interposed between an anode and acathode. Herein, the organic layer may include an emission layer andoptionally an auxiliary layer, and the auxiliary layer may include atleast one layer selected from, for example a hole injection layer, ahole transport layer, an electron blocking layer, an electron transportlayer, an electron injection layer, and a hole blocking layer in orderto improve efficiency and stability of an organic light emitting diode.

Performance of an organic light emitting diode may be affected bycharacteristics of the organic layer, and among them, may be mainlyaffected by an organic material of the organic layer.

Particularly, development for an organic material being capable ofincreasing hole and electron mobility and simultaneously increasingelectrochemical stability is needed so that the organic light emittingdiode may be applied to a large-size flat panel display.

DISCLOSURE Technical Problem

One embodiment provides an organic alloy applicable for an organicoptoelectric device.

Another embodiment provides organic optoelectric device including theorganic alloy.

Yet another embodiment provides a display device including the organicoptoelectric device.

Technical Solution

According to one embodiment, provided is an organic alloy for an organicoptoelectric device that is an organic alloy of at least two kinds oforganic compounds, the at least two kinds of organic compounds includesa first organic compound and a second organic compound, a differencebetween evaporation temperatures of the first organic compound and thesecond organic compound is less than or equal to about 20° C. at lessthan or equal to about 10⁻³ tom and a light emitting wavelength of theorganic alloy is different from light emitting wavelengths of the firstorganic compound, the second organic compound, and a simple mixture ofthe first organic compound and the second organic compound.

According to another embodiment, provided is an organic optoelectricdevice including an anode and a cathode facing each other, at least oneorganic layer interposed between the anode and the cathode, wherein theorganic layer includes the organic alloy.

According to yet another embodiment, a display device including theorganic optoelectric device is provided.

Advantageous Effects

The present invention may provide an organic alloy having differentcharacteristics from those of a conventional single organic compound anda simple mixture thereof and realize an organic optoelectric devicehaving high efficiency and long life-span by applying the organic alloyto the organic optoelectric device.

DESCRIPTION OF DRAWINGS

FIGS. 1 and 2 are cross-sectional views showing organic light emittingdiodes according to each embodiment the present invention,

FIG. 3 is a graph showing light emitting characteristics of an organicalloy according to Example 1 and organic materials according toComparative Examples 1 to 3 depending on a wavelength, and

FIG. 4 is a graph showing light emitting characteristics of an organicalloy according to Example 2 and organic materials according toComparative Examples 1, 4 and 5 depending on a wavelength.

BEST MODE

Hereinafter, embodiments of the present invention are described indetail. However, these embodiments are exemplary, and this disclosure isnot limited thereto.

As used herein, when a definition is not otherwise provided, the term“substituted” refers to one substituted with deuterium, a halogen, ahydroxy group, an amino group, a substituted or unsubstituted C1 to C30amine group, a nitro group, a substituted or unsubstituted C1 to C40silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, afluoro group, a C1 to C10 trifluoroalkyl group such as a trifluoromethylgroup and the like, or a cyano group, instead of at least one hydrogenof a substituent or a compound.

In addition, two adjacent substituents of the substituted halogen,hydroxy group, amino group, substituted or unsubstituted C1 to C20 aminegroup, nitro group, substituted or unsubstituted C3 to C40 silyl group,C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkylgroup, C2 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30heterocyclic group, C1 to C20 alkoxy group, fluoro group, C1 to C10trifluoroalkyl group such as trifluoromethyl group and the like, orcyano group may be fused to each other to form a ring. For example, thesubstituted C6 to C30 aryl group may be fused with another adjacentsubstituted C6 to C30 aryl group to form a substituted or unsubstitutedfluorene ring.

In the present specification, when specific definition is not otherwiseprovided, the term “hetero” refers to one including 1 to 3 hetero atomsselected from N, O, S, P and Si, and remaining carbons in one compoundor substituent.

In the present specification, when a definition is not otherwiseprovided, the term “alkyl group” may refer to an aliphatic hydrocarbongroup. The alkyl group may refer to “a saturated alkyl” without anydouble bond or triple bond.

The alkyl group may be a C1 to C30 alkyl group. More specifically, thealkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group.For example, a C1 to C4 alkyl group includes 1 to 4 carbons in alkylchain, and may be selected from methyl, ethyl, propyl, iso-propyl,n-butyl, iso-butyl, sec-butyl, and t-butyl.

Specific examples of the alkyl group may be a methyl group, an ethylgroup, a propyl group, an isopropyl group, a butyl group, an isobutylgroup, a t-butyl group, a pentyl group, a hexyl group, a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, andthe like.

In the present specification, the term “aryl group” refers to asubstituent including all element of the cycle having p-orbitals whichform conjugation, and may be monocyclic or fused ring polycyclic (i.e.,rings sharing adjacent pairs of carbon atoms) functional group.

As used herein, the term “heterocyclic group” may refer to cyclic groupincluding 1 to 3 hetero atoms selected from N, O, S, P and Si, andremaining carbons in a cyclic group. The heterocyclic group may be afused ring where each ring may include the 1 to 3 heteroatoms.

More specifically, the substituted or unsubstituted C6 to C30 aryl groupand/or the substituted or unsubstituted C2 to C30 heterocyclic group maybe a substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted anthracenylgroup, a substituted or unsubstituted phenanthryl group, a substitutedor unsubstituted naphthacenyl group, a substituted or unsubstitutedpyrenyl group, a substituted or unsubstituted biphenyl group, asubstituted or unsubstituted p-terphenyl group, a substituted orunsubstituted m-terphenyl group, a substituted or unsubstitutedchrysenyl group, a substituted or unsubstituted triphenylenyl group, asubstituted or unsubstituted perylenyl group, a substituted orunsubstituted indenyl group, a substituted or unsubstituted furanylgroup, a substituted or unsubstituted thiophenyl group, a substituted orunsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolylgroup, a substituted or unsubstituted imidazolyl group, a substituted orunsubstituted triazolyl group, a substituted or unsubstituted oxazolylgroup, a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted oxadiazolyl group, a substituted or unsubstitutedthiadiazolyl group, a substituted or unsubstituted pyridyl group, asubstituted or unsubstituted pyrimidinyl group, a substituted orunsubstituted pyrazinyl group, a substituted or unsubstituted triazinylgroup, a substituted or unsubstituted benzofuranyl group, a substitutedor unsubstituted benzothiophenyl group, a substituted or unsubstitutedbenzimidazolyl group, a substituted or unsubstituted indolyl group, asubstituted or unsubstituted quinolinyl group, a substituted orunsubstituted isoquinolinyl group, a substituted or unsubstitutedquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, asubstituted or unsubstituted naphthyridinyl group, a substituted orunsubstituted benzoxazinyl group, a substituted or unsubstitutedbenzthiazinyl group, a substituted or unsubstituted acridinyl group, asubstituted or unsubstituted phenazinyl group, a substituted orunsubstituted phenothiazinyl group, a substituted or unsubstitutedphenoxazinyl group, a substituted or unsubstituted fluorenyl group, asubstituted or unsubstituted dibenzofuranyl group, a substituted orunsubstituted dibenzothiophenyl group, a substituted or unsubstitutedcarbazole group, a combination thereof, or a fused group of thecombination, but are limited thereto.

In the specification, hole characteristics refer to characteristicscapable of donating an electron to form a hole when electric field isapplied, and characteristics that hole formed in the anode is easilyinjected into the emission layer and transported in the emission layerdue to conductive characteristics according to HOMO level.

In addition, electron characteristics refer to characteristics capableof accepting an electron when electric field is applied, andcharacteristics that electron formed in the cathode is easily injectedinto the emission layer and transported in the emission layer due toconductive characteristics according to LUMO level.

Hereinafter, an organic alloy for an organic optoelectric deviceaccording to one embodiment is described.

The organic alloy is a material obtained by pre-treating more than twosingle organic compounds and a chemical interaction among the singleorganic compounds may be provided due to the pre-treatment. Thepre-treating may be a heat treatment such as heating and sublimationfollowed by cooling, but is not limited thereto.

When the more than two single organic compounds include first and secondorganic compounds, the first and second organic compounds may have anevaporation temperature within the same or a predetermined range.Herein, the evaporation temperature indicates a temperature at which thefirst and second organic compounds may be deposited on a substrate at apredetermined rate under high vacuum of less than or equal to about 10⁻³Torr, for example, an average temperature when the first and secondorganic compounds are thermally evaporated to be about 300 nm to about800 nm thick at a rate of about 0.5 to about 2 Å/sec under high vacuumof less than or equal to about 10⁻³ Torr.

For example, the difference between evaporation temperatures of thefirst organic compound and the second organic compound may be less thanor equal to about 20° C. at less than or equal to about 10⁻³ torr.Within the range, a difference between evaporation temperatures of thefirst organic compound and the second organic compound may be about 0°C. to 10° C. and specifically about 0° C. to about 5° C.

The organic alloy has a chemical interaction among more than two singleorganic compounds as described above and thus, different intrinsiccharacteristics from the single organic compounds and their simplemixture having no chemical interaction among single organic compounds.Herein, the simple mixture is obtained by physically mixing singleorganic compounds without any pre-treatment. In other words, when themore than two single organic compounds include the first and secondorganic compounds, the organic alloy of the first and second organiccompounds may have different intrinsic characteristics from those of thefirst organic compound, the second organic compound, and a simplemixture thereof, while the single mixture of the first and secondorganic compounds show characteristics of the first organic compound,the second organic compound, or a combination thereof.

For example, the light emitting wavelength of the organic alloy may bedifferent from light emitting wavelengths of the first organic compound,the second organic compound, and a simple mixture thereof.

The organic alloy may release new energy and emit light by a new energybandgap between a high HOMO energy level and a low LUMO energy level ofthe first and second organic compounds due to intermolecular electrontransfer system of the two organic compounds. For example, the energybandgap of the organic alloy may be an energy difference between LUMOenergy level of the first organic compound and HOMO energy level of thesecond organic compound or between LUMO energy level of the secondorganic compound and HOMO energy level of the first organic compound. Onthe other hand, the simple mixture of the first and second organiccompounds may have either an energy bandgap between LUMO energy and HOMOenergy of the first organic compound or a bandgap between LUMO energyand HOMO energy of the second organic compound. Herein, the organicalloy may have a smaller or larger bandgap than that of the firstorganic compound, the second organic compound, and the simple mixturethereof. Accordingly, the light emitting wavelength of the organic alloymay be different from light emitting wavelengths of the first organiccompound, the second organic compound, and a simple mixture thereof.

A maximum light emitting wavelength (λ_(max)) of the organic alloy maybe shifted greater than or equal to about 20 nm compared with a maximumlight emitting wavelength of the simple mixture of the first and secondorganic compounds, for example, shifted greater than or equal to about20 nm toward a long wavelength region.

In addition, the organic alloy may have a different color from those ofthe first organic compound, the second organic compound, and the simplemixture thereof. For example, the organic alloy may have a color with alonger wavelength region than those of the first organic compound, thesecond organic compound, and the simple mixture thereof.

Furthermore, the organic alloy may have a different glass transitiontemperature (Tg) from that of the first organic compound, the secondorganic compound, and the simple mixture thereof. In addition, theorganic alloy may have a different crystallization temperature (Tc) fromthat of the first organic compound, the second organic compound, and thesimple mixture thereof. In addition, the organic alloy may have adifferent melting point (Tm) from that of the first organic compound,the second organic compound, and the simple mixture thereof. Since theglass transition temperature (Tg), the crystallization temperature (Tc),and the melting point (Tm) show inherent thermodynamic characteristicsof a molecule, the compounds having the different glass transitiontemperature (Tg), the different crystallization temperature (Tc) and thedifferent melting point (Tm) may be different compounds.

The organic alloy may have inherent thermodynamic characteristics suchas the glass transition temperature (Tg), the crystallizationtemperature (Tc), and the melting point (Tm), which may be substantiallyconstant within an error range. The error range may vary depending on ameasurement condition, for example, may be within about ±5° C. andspecifically, within about ±2° C. These thermodynamic characteristicsmay be different from those of the simple mixture of the first andsecond organic compounds having no inherent thermodynamiccharacteristics.

The organic alloy may be pre-treated in various methods, for example, ina method of heat-treating the first and second organic compounds atgreater than or equal to an evaporation temperature and liquidating orgasifying the first and second organic compounds and then, cooling andsolidifying the heat-treated compounds. The first and second organiccompounds may be melted liquid or gasified vapor at the evaporationtemperature, and the pre-treated organic alloy may be a solid like amass or powder. In addition, the organic alloy obtained as a solid massmay be additionally physically ground with a blender and the like.

The organic alloy is a resulting material obtained through theaforementioned pre-treatment and may be supplied by using one source toform a thin film. Accordingly, the deposition process may become simplewithout a control process required when more than two organic compoundsare respectively supplied by using separate sources.

In addition, the organic alloy is a resulting material obtained throughthe aforementioned pre-treatment and thus, may secure uniformity andconsistency for deposition compared with the more than two singleorganic compounds supplied by using more than two separate sources ortheir simple mixture of supplied by using one single source.Accordingly, when a plurality of thin films are formed through acontinuous process, the organic alloy may be used to continuouslyproduce the thin films including components in a substantiallyequivalent ratio and thus, increase reproducibility and reliability ofthe thin films.

The first and second organic compounds may include any material havingan evaporation temperature for pre-treatment at a predeterminedtemperature without a particular limit, for example, a compound havingelectron characteristics and a compound having hole characteristics toimprove mobility of electrons and holes. For example, the first organiccompound may be a compound having relatively strong electroncharacteristics, and the second organic compound may be a compoundhaving relatively strong hole characteristics, and thus, the organicalloy of the first organic compound having relatively strong electroncharacteristics and the second organic compound having relatively stronghole characteristics may have bipolar characteristics.

The first organic compound is a compound having relatively strongelectron characteristics, for example a compound represented by thefollowing Chemical Formula 1.

In the above Chemical Formula 1,

Z is independently N or CR^(a),

at least one of Z is N,

R¹ to R¹⁰ and R^(a) are independently hydrogen, deuterium, a substitutedor unsubstituted C1 to C10 alkyl group, a substituted or unsubstitutedC6 to C12 aryl group, or a combination thereof,

In the above Chemical Formula 1, the total number of 6-membered ringssubstituting the triphenylene group is less than or equal to 6,

L is a substituted or unsubstituted phenylene group, a substituted orunsubstituted biphenylene group or a substituted or unsubstitutedterphenylene group,

n1 to n3 are independently 0 or 1, and n1+n2+n3≧1.

Herein, the 6-membered rings substituting the triphenylene groupindicate all the 6-membered rings directly or indirectly linked to thetriphenylene group and include 6-membered rings including a carbon atom,a nitrogen atom, or a combination thereof.

The first organic compound may be represented by for example thefollowing Chemical Formula 1-I or 1-II, depending on the bondingposition of the triphenylene group.

In the above Chemical Formula 1-I or 1-II, Z, R¹ to R¹⁰, L and n1 to n3are the same as described above.

The first organic compound includes the triphenylene group and at leastone nitrogen-containing heterocyclic group.

The first organic compound includes at least one nitrogen-containingring and thereby, may have a structure of easily accepting electronswhen an electric field is applied thereto and thus, decrease a drivingvoltage of an organic optoelectric device including the first organiccompound.

In addition, the first organic compound has a bipolar structure byincluding both a triphenylene structure of easily accepting holes and anitrogen-containing ring moiety of easily accepting electrons and mayappropriately balance a flow of the holes and the electrons, andaccordingly, improve efficiency of an organic optoelectric device whenapplied thereto.

The first organic compound represented by the above Chemical Formula 1has at least one kink structure as a center of an arylene group and/or aheterocyclic group.

The kink structure is a structure that a linking moiety of the arylenegroup and/or the heterocyclic group is not a linear structure. Forexample, as for phenylene, ortho phenylene (o-phenylene) and metaphenylene (m-phenylene) have the kink structure where a linking moietydoes not form a linear structure, while para phenylene (p-phenylene) hasno kink structure because where a linking moiety forms a linearstructure.

In the above Chemical Formula 1, the kink structure may be formed as acenter of a linking group (L) and/or an arylene group/a heterocyclicgroup.

For example, when n1 in the above Chemical Formula 1 is 0, that is,there is no linking group (L), a kink structure may be formed as acenter of an arylene group/a heterocyclic group, and for example, thecompound may be represented by the following Chemical Formula 1a or 1 b.

In the above Chemical Formula 1a or 1b, Z, R¹ to R¹⁰ and L are the sameas described above.

For example, when n1 in the above Chemical Formula 1 is 1, a kinkstructure is formed as a center of a linking group (L), and for example,the L is may be a substituted or unsubstituted phenylene having the kinkstructure, a substituted or unsubstituted biphenylene group having thekink structure, or a substituted or unsubstituted terphenylene grouphaving the kink structure. The L may be selected from, for examplesubstituted or unsubstituted groups listed in the following Group 1.

In the Group 1,

R¹⁵ to R⁴² are independently hydrogen, deuterium, a substituted orunsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30heterocycloalkyl group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C2 to C30 heterocyclic group, asubstituted or unsubstituted amine group, a substituted or unsubstitutedC6 to C30 arylamine group, a substituted or unsubstituted C6 to C30heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxygroup, a halogen, a halogen-containing group, a cyano group, a hydroxylgroup, an amino group, a nitro group, a carboxyl group, a ferrocenylgroup, or a combination thereof.

The first organic compound may have at least two kink structures and forexample, two to four kink structures.

The first organic compound may appropriately localize charges andcontrol a conjugation-system flow due to the above kink structure, andthus improve a life-span of an organic optoelectric device to which thecomposition is applied.

In addition, in Chemical Formula 1, the number of R¹ to R⁶, that is thetotal number of 6-membered rings substituting the triphenylene group islimited to be less than or equal to 6, and thereby thermal decompositionof the compound by a high temperature during a deposition process may bedecreased.

In addition, the first organic compound may be effectively preventedfrom stacking depending on the structure and decrease process stabilityand simultaneously, a deposition temperature. This stacking preventioneffect may be further increased when the compound includes the linkinggroup (L) of the above Chemical Formula 1.

The first organic compound may be, for example represented by one of thefollowing Chemical Formulae 1c to it.

In the above Chemical Formulae 1c to it,

Z and R¹ to R¹⁰ are independently the same as described above, and

R⁶⁰ to R⁷⁷ are independently hydrogen, deuterium, a substituted orunsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30heterocycloalkyl group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C2 to C30 heterocyclic group, asubstituted or unsubstituted amine group, a substituted or unsubstitutedC6 to C30 arylamine group, a substituted or unsubstituted C6 to C30heteroarylamine group, a substituted or unsubstituted C1 to C30 alkoxygroup, a halogen, a halogen-containing group, a cyano group, a hydroxylgroup, an amino group, a nitro group, a carboxyl group, a ferrocenylgroup, or a combination thereof.

The first organic compound may be, for example, a compound listed in thefollowing Group 2 but is not limited thereto.

At least one or more kinds of the first organic compound may be used.

The second organic compound may be a compound having relatively stronghole characteristics, for example, a compound represented by thefollowing Chemical Formula 2.

In the above Chemical Formula 2,

Y¹ and Y² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC2 to C20 alkenylene group, a substituted or unsubstituted C6 to C30arylene group, a substituted or unsubstituted C2 to C30 heterocyclicgroup, or a combination thereof,

Ar¹ and Ar² are a substituted or unsubstituted C6 to C30 aryl group, asubstituted or unsubstituted C2 to C30 heterocyclic group, or acombination thereof, and

R¹¹ to R¹³, R⁴³ and R⁴⁴ are independently hydrogen, deuterium, asubstituted or unsubstituted C1 to C20 alkyl group, a substituted orunsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 toC50 heterocyclic group, or a combination thereof.

The second organic compound is a compound having bipolar characteristicsin which hole characteristics are relatively stronger than electroncharacteristics and thus, increases charge mobility and stability byforming an organic alloy with the first organic compound andresultantly, may improve luminous efficiency and life-spancharacteristics.

Ar¹ and Ar² of the above Chemical Formula 2 are substitutents havinghole or electron characteristics, and may be independently for example asubstituted or unsubstituted phenyl group, a substituted orunsubstituted biphenyl group, a substituted or unsubstituted terphenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted anthracenyl group, substituted or unsubstitutedtriphenylenyl group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted benzofuranyl group, a substituted orunsubstituted benzothiophenyl group, a substituted or unsubstitutedfluorenyl group, a substituted or unsubstituted pyridyl group, asubstituted or unsubstituted pyrimidinyl group, a substituted orunsubstituted pyrazinyl group, a substituted or unsubstituted triazinylgroup, a substituted or unsubstituted dibenzofuranyl group, asubstituted or unsubstituted dibenzothiophenyl group, or a combinationthereof.

At least one of Ar¹ and Ar² of the above Chemical Formula 2 may be forexample substituents having electron characteristics, and may be forexample substituents represented by the following Chemical Formula A.

In the above Chemical Formula A,

Z is independently N or CR^(b),

A1 and A2 are independently a substituted or unsubstituted C6 to C30aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group,or a combination thereof,

at least one of the Z, A1 and A2 includes N, and

a and b are independently 0 or 1.

The substituent represented by the above Chemical Formula A may be forexample one of functional groups listed in the following Group 3.

In addition, at least one of Ar¹ and Ar² of the above Chemical Formula 2may be, for example a substituent having hole characteristics, and maybe, for example substituents listed in the following Group 4.

The compound represented by the above Chemical Formula 2 may be, forexample selected from compounds listed in the following Group 5, but isnot limited thereto.

At least one or more kinds of the second organic compound may be used.

The above first and second organic compounds may be variously combinedto prepare various organic alloys. For example the first organiccompound may be at least one of compounds listed in the following GroupA, and the second organic compound may be at least one of compoundslisted in the following Group B, but they are not limited thereto.

As described above, the first organic compound is a compound havingrelatively strong electron characteristics, the second organic compoundis a compound having relatively strong hole characteristics, and theyare pre-treated to form an organic alloy to increase mobility ofelectrons and holes and thus, to remarkably improve luminous efficiencycompared with when the first compound or the second compound is used atalone.

When the single material having biased toward electron characteristicsor biased toward hole characteristics is used to form an emission layer,excitons may be relatively more formed at an interface of an emissionlayer and the electron transport layer (ETL) or hole transport layer(HTL). As a result, the excitons in the emission layer may interact withcharges at the interface of the electron transport layer (ETL) or thehole transport layer (HTL) and thus, cause a roll-off of sharplydeteriorating efficiency and also, sharply deteriorate light emittinglife-span characteristics. In order to solve this problem, the organicalloy of the first organic compound and the second organic compound isintroduced into the emission layer to manufacture a device balancingcarriers in the emission layer, so that a light emitting area may not bebiased toward either the electron transport layer (ETL) or holetransport layer (HTL) and thus, remarkably improving roll-off andsimultaneously life-span characteristics.

The organic alloy may be obtained by using the first organic compoundand the second organic compound in a mole ratio, for example about 1:10to about 10:1. As another examples, the organic alloy may be obtained byusing the first organic compound and the second organic compound in amole ratio of about 1:4 to about 4:1, or in a mole ratio of about 1:1.

Within the range, bipolar characteristics may be realized moreefficiently and efficiency and life-span may be improved.

The organic alloy may be obtained by pre-treating the above firstorganic compound and second organic compound, or may be obtained bypre-treating at least one kind of an organic compound besides the abovefirst organic compound and second organic compound.

The organic alloy may be used as an organic material for an organicoptoelectric device, and may be used as, for example a light emittingmaterial, a light absorbing material, a charge transport material, acharge injection material, a charge blocking material, or a combinationthereof.

For example, the organic alloy may be used as a light emitting materialfor an organic optoelectric device. Herein, the organic alloy may beused as a host, and may further include at least one kind of a dopant.The dopant may be a red, green, or blue dopant, for example aphosphorescent dopant.

The dopant is mixed with the organic alloy in a small amount to causelight emission, and may be generally a material such as a metal complexthat emits light by multiple excitation into a triplet or more. Thedopant may be, for example an inorganic, organic, or organic/inorganiccompound, and one or more kinds thereof may be used.

Examples of the phosphorescent dopant may be an organic metal compoundincluding Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, ora combination thereof. The phosphorescent dopant may be, for example acompound represented by the following Chemical Formula Z, but is notlimited thereto.

L₂MX  [Chemical Formula Z]

In the above Chemical Formula Z, M is a metal, and L and X are the sameor different, and are a ligand to form a complex compound with M.

The M may be, for example Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co,Ni, Ru, Rh, Pd, or a combination thereof, and the L and X may be, forexample a bidendate ligand.

The organic material may form a film using a dry film-forming methodsuch as chemical vapor deposition or a solution process.

Hereinafter, an organic optoelectric device to which the organicmaterial is applied is described.

The organic optoelectric device may be any device to convert electricalenergy into photoenergy and vice versa without particular limitation,and may be, for example an organic photoelectric device, an organiclight emitting diode, an organic solar cell, and an organicphoto-conductor drum.

The organic optoelectric device includes an anode and a cathode facingeach other, and at least one organic layer interposed between the anodeand the cathode, wherein the organic layer includes the above organicmaterial.

Herein, an organic light emitting diode as one example of an organicoptoelectric device is described referring to drawings.

FIGS. 1 and 2 are cross-sectional views of each organic light emittingdiode according to one embodiment.

Referring to FIG. 1, an organic light emitting diode 100 according toone embodiment includes an anode 120 and a cathode 110 facing each otherand an organic layer 105 interposed between the anode 120 and cathode110.

The anode 120 may be made of a conductor having a large work function tohelp hole injection, and may be for example metal, metal oxide and/or aconductive polymer. The anode 120 may be a metal such as nickel,platinum, vanadium, chromium, copper, zinc, gold, and the like or analloy thereof; metal oxide such as zinc oxide, indium oxide, indium tinoxide (ITO), indium zinc oxide (IZO), and the like; a combination ofmetal and oxide such as ZnO and Al or SnO₂ and Sb; a conductive polymersuch as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene)(PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

The cathode 110 may be made of a conductor having a small work functionto help electron injection, and may be for example metal, metal oxideand/or a conductive polymer. The cathode 110 may be for example a metalor an alloy thereof such as magnesium, calcium, sodium, potassium,titanium, indium, yttrium, lithium, gadolinium, aluminum silver, tin,lead, cesium, barium, and the like; a multi-layer structure materialsuch as LiF/Al, LiO₂/Al, LiF/Ca, LiF/Al and BaF₂/Ca, but is not limitedthereto.

The organic layer 105 may include an emission layer 130 including theabove organic material.

The emission layer 130 may include, for example the above organicmaterial.

Referring to FIG. 2, an organic light emitting diode 200 furtherincludes a hole auxiliary layer 140 as well as an emission layer 130.The hole auxiliary layer 140 may further increase hole injection and/orhole mobility between the anode 120 and emission layer 130 and blockelectrons. The hole auxiliary layer 140 may be, for example a holetransport layer (HTL), a hole injection layer (HIL), and/or an electronblocking layer (EBL), and may include at least one layer.

In one embodiment of the present invention, an organic light emittingdiode may further include an electron transport layer (ETL), an electroninjection layer (EIL), a hole injection layer (HIL), and the like, in anorganic layer 105 in FIG. 1 or FIG. 2.

The organic light emitting diodes 100 and 200 may be manufactured byforming an anode or a cathode on a substrate, forming an organic layerin accordance with a dry coating method such as evaporation, sputtering,plasma plating, and ion plating; and forming a cathode or an anodethereon.

The organic light emitting diode may be applied to an organic lightemitting diode (OLED) display.

MODE FOR INVENTION

Hereinafter, the embodiments are illustrated in more detail withreference to examples. These examples, however, are not in any sense tobe interpreted as limiting the scope of the invention.

Preparation of Single Organic Compound Synthesis of First OrganicCompound Compound A-33 Synthesis Example 1 Synthesis of Intermediate I-2

32.7 g (107 mmol) of 2-bromotriphenylene was dissolved in 0.3 L oftetrahydrofuran (THF) under a nitrogen atmosphere, 20 g (128 mmol) of3-chlorophenylboronic acid and 1.23 g (1.07 mmol) oftetrakis(triphenylphosphine)palladium were added thereto, and themixture was agitated. Subsequently, 36.8 g (267 mmol) of potassiumcarbonate saturated in water was added thereto, and the mixture washeated and refluxed at 80° C. for 24 hours. When the reaction wascomplete, water was added to the reaction solution, and the mixture wastreated with dichloromethane (DCM) for extraction and with anhydrousMgSO₄ to remove moisture and then, filtered and concentrated under areduced pressure. The obtained residue was separated and purifiedthrough flash column chromatography, obtaining 22.6 g (63%) of thecompound I-2.

HRMS (70 eV, EI+): m/z calcd for C24H15Cl: 338.0862. found: 338.

Elemental Analysis: C, 85%; H, 5%

Synthesis Example 2 Synthesis of Intermediate I-3

22.6 g (66.7 mmol) of the compound I-2 was dissolved in 0.3 L ofdimethylformamide (DMF) under a nitrogen atmosphere, 25.4 g (100 mmol)of bis(pinacolato)diboron, 0.54 g (0.67 mmol) of(1,1′-bis(diphenylphosphine)ferrocene)dichloropalladium (II), and 16.4 g(167 mmol) of potassium acetate were added thereto, and the mixture washeated and refluxed at 150° C. for 48 hours. When the reaction wascomplete, water was added to the reaction solution, and the mixture wasfiltered and dried in a vacuum oven. The obtained residue was separatedand purified through flash column chromatography, obtaining 18.6 g (65%)of a compound I-3.

HRMS (70 eV, EI+): m/z calcd for C30H27BO2: 430.2104. found: 430.

Elemental Analysis: C, 84%; H, 6%

Synthesis Example 3 Synthesis of Intermediate I-6

50 g (116 mmol) of the compound I-3 was dissolved in 0.5 L oftetrahydrofuran (THF) under a nitrogen atmosphere, 39.4 g (139 mmol) of1-bromo-3-iodobenzene and 1.34 g (1.16 mmol) oftetrakis(triphenylphosphine)palladium were added thereto, and themixture was agitated. Subsequently, 40.1 g (290 mmol) of potassiumcarbonate saturated in water was added thereto, and the mixture washeated and refluxed at 80° C. for 12 hours. When the reaction wascomplete, water was added to the reaction solution, and the mixture wastreated dichloromethane (DCM) for extraction and treated with anhydrousMgSO₄ to remove moisture and then, filtered and concentrated under areduced pressure. The obtained residue was separated and purifiedthrough flash column chromatography, obtaining 42.6 g (80%) of thecompound I-6.

HRMS (70 eV, EI+): m/z calcd for C30H19Br: 458.0670. found: 458.

Elemental Analysis: C, 78%; H, 4%

Synthesis Example 4 Synthesis of Intermediate I-7

40 g (87.1 mmol) of the compound I-6 was dissolved in 0.3 L ofdimethylformamide (DMF) under a nitrogen atmosphere, 26.5 g (104 mmol)of bis(pinacolato)diboron, 0.71 g (0.87 mmol) of(1,1′-bis(diphenylphosphine)ferrocene)dichloropalladium (II) and 21.4 g(218 mmol) of potassium acetate were added thereto, and the mixture washeated and refluxed at 150° C. for 26 hours. When the reaction wascomplete, water was added to the reaction solution, and the mixture wasfiltered and dried in a vacuum oven. The obtained residue was separatedand purified through flash column chromatography, obtaining 34 g (77%)of the compound I-7.

HRMS (70 eV, EI+): m/z calcd for C36H31BO2: 506.2417. found: 506.

Elemental Analysis: C, 85%; H, 6%

Synthesis Example 5 Synthesis of Compound A-33

20 g (39.5 mmol) of the compound I-7 was dissolved in 0.2 L oftetrahydrofuran (THF) under a nitrogen atmosphere, 10.6 g (39.5 mmol) of2-chloro-4,6-diphenyl-1,3,5-triazine and 0.46 g (0.4 mmol) oftetrakis(triphenylphosphine)palladium were added thereto, and themixture was agitated. Subsequently, 13.6 g (98.8 mmol) of potassiumcarbonate saturated in water was added thereto, and the mixture washeated and refluxed at 80° C. for 23 hours. When the reaction wascomplete, water was added to the reaction solution, and the mixture wastreated with dichloromethane (DCM) for extraction and with anhydrousMgSO4 to remove moisture and then, filtered and concentrated under areduced pressure. The obtained residue was separated and purifiedthrough flash column chromatography, obtaining 17.9 g (74%) of thecompound A-33.

HRMS (70 eV, EI+): m/z calcd for C45H29N3: 611.2361. found: 611.

Elemental Analysis: C, 88%; H, 5%

The compound A-33 had an evaporation temperature of about 226±10° C.under less than or equal to 10⁻³ Torr.

Synthesis Example 1 of Second Organic Compound Compound B-10

First Step: Synthesis of Compound J

26.96 g (81.4 mmol) of N-phenyl carbazole-3-boronic acid pinacolate,23.96 g (97.36 mmol) of 3-bromo carbazole, and 230 mL of tetrahydrofuranwere mixed with 100 ml of a 2 M-potassium carbonate aqueous solution,and the mixture was heated and refluxed under a nitrogen current for 12hours. When the reaction was complete, a solid produced by pouringmethanol to the reactant was filtered and dissolved in chlorobenzeneagain, activated carbon and anhydrous magnesium sulfate were addedthereto, and the mixture was agitated. The solution was filtered andrecrystallized by using chlorobenzene and methanol, obtaining 22.6 g ofa compound J (a yield: 68%).

HRMS (70 eV, EI+): m/z calcd for C30H20N2: 408.16. found: 408.

Elemental Analysis: C, 88%; H, 5%

Second Step: Synthesis of Compound B-10

22.42 g (54.88 mmol) of the compound J, 20.43 g (65.85 mmol) of2-bromo-4,6-diphenylpyridine, and 7.92 g (82.32 mmol) oftertiarybutoxysodium were dissolved in 400 ml of toluene, and 1.65 g(1.65 mmol) of palladium dibenzylideneamine and 1.78 g (4.39 mmol) oftri-tertiarybutylphosphine (P(t-Bu)₃) were added in a dropwise fashion.The reaction solution was heated 110° C. and agitated under a nitrogencurrent for 12 hours. When the reaction was complete, a solid producedby pouring methanol to the reactant was filtered and dissolved inchlorobenzene again, activated carbon and anhydrous magnesium sulfatewere added thereto, and the mixture was agitated. The solution wasfiltered and recrystallized by using chlorobenzene and methanol,obtaining 28.10 g of a compound B-10 (a yield: 80%).

HRMS (70 eV, EI+): m/z calcd for C47H31N3: 637.25. found: 637.

Elemental Analysis: C, 89%; H, 5%

The compound B-10 had an evaporation temperature of about 225±10° C.under less than or equal to 10⁻³ Torr.

Synthesis Example 2 of Second Organic Compound Compound B-43

12.33 g (30.95 mmol) of biphenylcarbazolyl bromide, 12.37 g (34.05 mmol)of biphenylcarbazolylboronic acid, and 12.83 g (92.86 mmol) of potassiumcarbonate, and 1.07 g (0.93 mmmol) oftetrakis-(triphenylphosphine)palladium (0) were suspended in 120 ml oftoluene and 50 ml of distilled water, and the suspended solution wasrefluxed and agitated for 12 hours. Subsequently, the reactant wasextracted with dichloromethane and distilled water, and an organic layerobtained therefrom was filtered with silica gel. Subsequently, anorganic solution therein was removed, and a solid product therefrom wasrecrystallized with dichloromethane and n-hexane, obtaining a compoundB-43 18.7 g (a yield: 92%).

HRMS (70 eV, EI+): m/z calcd for C48H32N2: 636.26. found: 636.

Elemental Analysis: C, 91%; H, 5%

The compound B-43 had an evaporation temperature of about 232±10° C.under less than or equal to 10⁻³ Torr.

Example Preparation of Organic Alloy Example 1 Organic Alloy of CompoundA-33 and Compound B-10

A powder-type organic alloy was obtained by putting the compound A-33and the compound B-10 in a mole ratio of 1:1 in a vacuum chamber of lessthan or equal to 10⁻³ Torr, melting the compound A-33 and the compoundB-10 by increasing temperature of the vacuum chamber, solidifying themby cooling down to room temperature of 25° C., and grinding the solidwith a blender.

Example 2 Organic Alloy of Compound A-33 and Compound B-43

A powder-type organic alloy was obtained by putting the compound A-33and the compound B-43 in a mole ratio of 1:1 in a vacuum chamber of lessthan or equal to 10⁻³ Torr, melting the compound A-33 and the compoundB-43 by increasing temperature of the vacuum chamber, solidifying themby cooling down to room temperature of 25° C., and grinding the solidwith a blender.

Comparative Example Preparation of Simile Compound and Simple MixtureComparative Example 1 Single Compound A-33

A powder-type compound A-33 was prepared by grinding the compound A-33according to Synthesis Example 5 with a blender at room temperature (25°C.).

Comparative Example 2 Single Compound B-10

The powder-type compound B-10 was prepared by grinding the compound B-10according to Synthesis Example 1 of a second organic compound attemperature (25° C.) with a blender.

Comparative Example 3 Simple Mixture of Compound A-33 and Compound B-10

The compound A-33 according to Synthesis Example 5 and the compound B-10according to Synthesis Example 1 of a second organic compound werephysically ground in a mole ratio of 1:1 with a blender, obtaining asimple mixture.

Comparative Example 4 Single Compound B-43

A powder-type compound B-43 was obtained by grinding the compound B-43according to Synthesis Example 2 of a second organic compound at roomtemperature (25° C.) with a blender.

Comparative Example 5 Simple Mixture of Compound A-33 and Compound B-43

The compound A-33 according to Synthesis Example 5 and the compound B-43according to Synthesis Example 1 of a second organic compound werephysically ground in a mole ratio of 1:1 at room temperature (25° C.)with a blender, preparing a simple mixture.

Evaluation Evaluation 1

Optical properties of the organic alloys according to Examples 1 and 2and the organic materials according to Comparative Examples 1 to 5 wereevaluated. The optical properties were evaluated by measuringphotoluminescence (PL) spectrum of powders of the organic alloysaccording to Examples 1 and 2 and the organic materials according toComparative Examples 1 to 5 with a Fluorescence spectrophotometer(F-4500, Hitachi). The powders were used as a sample, and herein, asolid sample holder of 650-0161 (Hitachi) was used as a PL holder.

The results are illustrated referring to FIGS. 3 and 4 and the followingTables 1 and 2.

FIG. 3 is a graph showing light emitting characteristics of the organicalloy according to Example 1 and the organic materials according toComparative Examples 1 to 3 depending on a wavelength, and FIG. 4 is agraph showing light emitting characteristics of the organic alloyaccording to Example 2 and the organic materials according toComparative Examples 1, 4, and 5 depending on a wavelength.

TABLE 1 Maximum light emitting wavelength λmax (nm) eV Example 1 4832.57 Comparative Example 1 411 3.02 Comparative Example 2 449 2.76Comparative Example 3 463 2.78

TABLE 2 Maximum light emitting wavelength λmax (nm) eV Example 2 4882.55 Comparative Example 1 411 3.02 Comparative Example 4 420 2.95Comparative Example 5 421 2.95

Referring to FIGS. 3 and 4 and the Tables 1 and 2, the organic alloy ofExample 1 showed different optical properties from the organic materialsaccording to Comparative Examples 1 to 3, and the organic alloy ofExample 2 showed different optical properties from the organic materialsaccording to Comparative Examples 1, 4, and 5.

In particular, the organic alloy of Example 1 showed inherent opticalproperties differing from those of the first organic compound A-33 andthe second organic compound B-10, for example, a maximum light emittingwavelength greater than or equal to about 20 nm moving toward a longwavelength, while the organic material of Comparative Example 3, thatis, a simple mixture of the first organic compound A-33 and the secondorganic compound B-10, showed optical properties of the first organiccompound A-33, the second organic compound B-10, or a combinationthereof.

Likewise, the organic alloy of Example 2 showed inherent opticalproperties differing from those of the first organic compound A-33 andthe second organic compound B-43, for example, a maximum light emittingwavelength greater than or equal to about 20 nm toward a longwavelength, while the organic material of Comparative Example 5, thatis, a simple mixture of the first organic compound A-33 and the secondorganic compound B-43 showed optical properties of the first organiccompound A-33, the second organic compound B-43, or a combinationthereof.

In addition, the organic alloy according to Example 1 showed inherentenergy level differing from those of the first organic compound A-33 andthe second organic compound B-10, while the organic material ofComparative Example 3, that is, a mixture of the first organic compoundA-33 and the second organic compound B-10, showed substantially similarenergy level to that of the first organic compound A-33 or the secondorganic compound B-10.

Likewise, the organic alloy of Example 2 showed inherent energy leveldiffering from those of first organic compound A-33 and the secondorganic compound B-43, while the organic material of Comparative Example5, that is, a simple mixture of the first organic compound A-33 and thesecond organic compound B-43 showed substantially similar energy levelto that of the first organic compound A-33 or the second organiccompound B-43.

Evaluation 2

Thermodynamic characteristics of the organic alloys of Examples 1 and 2and the organic materials of Comparative Examples 1 to 5 were evaluated.The thermodynamic characteristics of the organic alloys of Examples 1and 2 and the organic materials of Comparative Examples 1 to 5 weremeasured through differential scanning calorimetry by using DSC1(Mettler-Toledo Inc.).

The results are provided in Tables 3 and 4.

TABLE 3 Thermodynamic characteristics glass transition crystallizationtemperature temperature melting point (Tg, ° C.) (Tc, ° C.) (Tm, ° C.)Example 1 122 215 261 Comparative Example 1 — — 287 Comparative Example2 133 — — Comparative Example 3 133 — 255

TABLE 4 Thermodynamic characteristics glass transition crystallizationtemperature temperature melting point (Tg, ° C.) (Tc, ° C.) (Tm, ° C.)Example 2 116 184 260 Comparative Example 1 — — 287 Comparative Example4 122 — — Comparative Example 5 124 — 252

Referring to Tables 3 and 4, the organic alloy of Example 1 showeddifferent thermodynamic characteristics from those of the organicmaterials of Comparative Examples 1 to 3, and the organic alloy ofExample 2 showed different thermodynamic characteristics from theorganic materials according to Comparative Examples 1, 4, and 5.

In particular, the organic alloy of Example 1 showed inherentthermodynamic characteristics differing from those of the first organiccompound A-33, the second organic compound B-10, and a simple mixturethereof, while the organic material of Comparative Example 3, that is, asimple mixture of the first organic compound A-33 and the second organiccompound B-10 showed substantially similar thermodynamic characteristicsto those of the organic material of Comparative Example 2.

Likewise, the organic alloy of Example 2 showed different thermodynamiccharacteristics from those of the first organic compound A-33, thesecond organic compound B-43, and a simple mixture of the first organiccompound A-33 and the second organic compound B-43, while the organicmaterial of Comparative Example 5, a simple mixture of the first organiccompound A-33 and the second organic compound B-43 showed substantiallysimilar thermodynamic characteristics to those of the organic materialof Comparative Example 4, that is, the second organic compound B-43.

Evaluation 3

Consistency of the thermodynamic characteristics of the organic alloy ofExamples 1 and 2 and organic materials of Comparative Examples 3 and 5was evaluated. The consistency of thermodynamic characteristics wasevaluated by more than once measuring the thermodynamic characteristicsof Evaluation 2 and seeing if the measurements were constant.

The results are illustrated referring to Tables 5 and 6.

TABLE 5 Comparative Example 3 Example 1 #1 #2 #3 #1 #2 #3 #4 #5 Meltingpoint 259.9 255.2 280.1 260.7 261.4 260.1 261.3 261.3 (Tm, ° C.)

TABLE 6 Comparative Example 5 Example 2 #1 #2 #3 #1 #2 #3 #4 #5 Meltingpoint 259.9 280.3 276.3 260.3 261.5 260.2 262.1 261.9 (Tm, ° C.)

Referring to Tables 5 and 6, the organic alloys of Examples 1 and 2showed constant melting points within an error range of ±5° C.,especially, within an error range of ±2° C. over more than onemeasurement, while the organic materials of Comparative Examples 3 and 5showed largely different melting points over the measurements, forexample, within an error range of about 20° C. Accordingly, the organicalloys of Examples 1 and 2 showed more constant organic thermodynamiccharacteristics than a single organic compound or a simple mixturethereof.

Evaluation 4

Variation of the organic alloys according to Examples 1 and 2 with timeduring continuous process was evaluated.

The variation with time during continuous process was evaluated bycontinuously depositing the organic alloys of Examples 1 and 2 and theorganic materials of Comparative Examples 3 and 5 on a glass substrateto form a plurality of films and examining if single organic compoundsconstantly maintained a ratio in each film through a high performanceliquid chromatography (HPLC) analysis method. The variation with timeduring continuous process may be evaluated by seeing how much constantlya ratio among the components forming a film in a continuous process wasmanaged.

The results are provided in Tables 7 and 8.

In the following Table 7, three samples of the organic alloy accordingto Example 1 were prepared and used to form each thin film by repeatingthree times a continuous process, and the thin films were respectivelymarked as Examples 1-1, 1-2, and 1-3, and in the following Table 8, twosamples of the organic alloy according to Example 2 were prepared andused to form each thin film by three times or five times repeating acontinuous process and the films were respectively marked as Examples2-1 and 2-2.

TABLE 7 Variation with time during continuous process A-33 B-10Variation ratio (mol %) (mol %) A-33/B-10 with time (%) Example 1-1 152.2 47.8 1.09 2.67 2 52.6 47.4 1.11 3 52.8 47.2 1.12 Example 1-2 1 53.346.7 1.14 1.90 2 53.5 46.5 1.15 3 53.8 46.2 1.16 Example 1-3 1 53.1 46.91.13 2.90 2 53.7 46.3 1.16 3 53.8 46.2 1.16 Comparative 1 50.7 49.3 1.0311.02 Example 3 2 53.4 46.6 1.14 3 53.6 46.4 1.16

TABLE 8 Variation with time during continuous process sample A-33 B-43A-33/B- Variation ratio No. (mol %) (mol %) 43 with time (%) Example 2-11 53.6 46.4 1.16 1.36 2 53.7 46.3 1.16 3 54.0 46.0 1.17 Example 2-2 154.3 46.7 1.19 0.79 2 54.5 45.5 1.20 3 54.5 45.5 1.20 4 54.5 45.5 1.20 554.5 45.5 1.20 Comparative 1 49.6 50.4 0.98 22.01 Example 5 2 53.5 46.51.15 3 55.7 44.3 1.26

Referring to Tables 7 and 8, the films formed of the organic alloysaccording to Examples 1 and 2 showed almost constant ratio among singleorganic compounds, that is, A-33/B-10 or A-33/B-43 compared with thethin films formed of the organic materials according to ComparativeExamples 3 and 5. Accordingly, a thin film formed of an organic alloymay be reproduced through a continuous process compared with a thin filmformed of a simple mixture.

Manufacture of Organic Light Emitting Diode Example 3

A glass substrate coated with a 1500 Å-thick ITO (Indium tin oxide) wascleaned with distilled water and an ultrasonic wave. When the glasssubstrate is cleaned with distilled water, glass substrate wasultrasonic wave-cleaned with a solvent such as isopropyl alcohol,acetone, methanol and the like and dried, and then, moved to a plasmacleaner, cleaned by using oxygen plasma for 10 minutes and to a vacuumdepositor. This ITO transparent electrode was used as an anode, a 700Å-thick hole injection layer (HIL) was formed on the ITO substrate byvacuum-depositingN4,N4′-diphenyl-N4,N4′-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4′-diamine(the compound A), and a hole transport layer (HTL) was formed bydepositing 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN)(the compound B) to be 50 Å thick and then,N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine(the compound C) to be 1020 Å thick on the injection layer. On the holetransport layer (HTL), a 400 Å-thick emission layer was formed byvacuum-depositing the organic alloy of Example 1 as a host doped with 10wt % of tris(4-methyl-2,5-diphenylpyridine)iridium (Ill) (the compoundD) as a dopant.

Subsequently, a 300 Å-thick electron transport layer (ETL) was formed onthe emission layer by vacuum-depositing8-(4-(4-(naphthalen-2-yl)-6-(naphthalen-3-yl)-1,3,5-triazin-2-yl)phenyl)quinoline(the compound E) and simultaneously hydroxyquinoline lithium (Liq) in aratio of 1:1, and a cathode was formed on the electron transport layer(ETL) by sequentially vacuum-depositing Liq to be 15 Å thick and Al tobe 1200 Å thick, manufacturing an organic light emitting diode.

The organic light emitting diode had a structure of five-story organicthin films and specifically,

a structure of ITO/A 700 Å/B 50 Å/C 1020 Å/EML[organic alloy:D=X:10%]400 Å/E:Liq 300 Å/Liq 15 Å/Al 1200 Å.

(X=weight ratio)

Example 4

An organic light emitting diode was manufactured according to the samemethod as Example 3 except for using the organic alloy of Example 2instead of the organic alloy of Example 1.

Comparative Example 6

An organic light emitting diode was manufactured according to the samemethod as Example 3 except for using the organic material of ComparativeExample 1, that is, the compound A-33 as a single host instead of theorganic alloy of Example 1.

Comparative Example 7

An organic light emitting diode was manufactured according to the samemethod as Example 3 except for using the organic material of ComparativeExample 2, that is, the compound B-10 as a single host instead of theorganic alloy of Example 1.

Comparative Example 8

An organic light emitting diode was manufactured according to the samemethod as Example 3 except for using the organic material of ComparativeExample 3, that is, a simple mixture of the compound A-33 and thecompound B-10 instead of the organic alloy of Example 1.

Comparative Example 9

An organic light emitting diode was manufactured according to the samemethod as Example 3 except for using the organic material of ComparativeExample 4, that is, the compound B-43 as a single host instead of theorganic alloy of Example 1.

Comparative Example 10

An organic light emitting diode was manufactured according to the samemethod as Example 3 except for using the organic material of ComparativeExample 5, that is, a simple mixture of the compound A-33 and thecompound B-43 instead of the organic alloy of Example 1.

Evaluation 4

Luminous efficiency and life-span characteristics of the organic lightemitting diodes according to Examples 3 and 4 and Comparative Examples 6to 10 were evaluated.

The measurements were specifically performed in the following method,and the results were provided in the following Table 9 and Table 10.

(1) Measurement of Current Density Change Depending on Voltage Change

Current values flowing in the unit device of the manufactured organiclight emitting diodes were measured for, while increasing the voltagefrom 0 V to 10 V using a current-voltage meter (Keithley 2400), and themeasured current values were divided by an area to provide the results.

(2) Measurement of Luminance Change Depending on Voltage Change

Luminance of the manufactured organic light emitting diodes was measuredfor luminance, while increasing the voltage from 0 V to 10 V using aluminance meter (Minolta Cs-1000A).

(3) Measurement of Luminous Efficiency

Current efficiency (cd/A) at the same current density (10 mA/cm2) werecalculated by using the luminance, current density, and voltagesobtained from items (1) and (2).

(4) Measurement of Life-Span

Luminance (cd/m²) was maintained at 6000 cd/m² and a time at currentefficiency (cd/A) decreases to 97% was measured.

TABLE 9 Luminous Life- efficiency spanT97 Host (cd/A) (h) Example 3A-33 + B-10 organic 47.7 450 alloy Comparative Example 6 A-33 31.1 150Comparative Example 7 B-10 34.8 10 Comparative Example 8 A-33 + B-10simple 45.1 350 mixture

TABLE 10 Luminous Life- efficiency spanT97 Host (cd/A) (h) Example 4A-33 + B-43 organic 47.8 900 alloy Comparative Example 6 A-33 31.1 150Comparative Example 9 B-43 2.6 10 Comparative Example 10 A-33 + B-43simple 44.0 720 mixture

Referring to Tables 9 and 10, the organic light emitting diode ofExample showed equivalent or improved luminous efficiency and life-spancharacteristics compared with the organic light emitting diodes ofComparative Examples 6 to 8, and the organic light emitting diode ofExample 4 showed equivalent or improved luminous efficiency andlife-span characteristics compared with the organic light emittingdiodes of Comparative Examples 6, 9, and 10. Accordingly, an organiclight emitting diode using the organic alloy turned out to haveequivalent or improved performance compared with an organic lightemitting diode using a single organic compound or a simple mixturethereof.

While this invention has been described in connection with what ispresently considered to be practical exemplary embodiments, it is to beunderstood that the invention is not limited to the disclosedembodiments, but, on the contrary, is intended to cover variousmodifications and equivalent arrangements included within the spirit andscope of the appended claims. Therefore, the aforementioned embodimentsshould be understood to be exemplary but not limiting the presentinvention in any way.

DESCRIPTION OF SYMBOLS

-   -   100, 200: organic light emitting diode    -   105: organic layer    -   110: cathode    -   120: anode    -   130: emission layer    -   140: hole auxiliary layer

1. An organic alloy for an organic optoelectric device, which is anorganic alloy of at least two kinds of organic compounds, the at leasttwo kinds of organic compounds includes a first organic compound and asecond organic compound, a difference between evaporation temperaturesof the first organic compound and the second organic compound is lessthan or equal to 20° C. at less than or equal to 10⁻³ torr, and a lightemitting wavelength of the organic alloy is different from lightemitting wavelengths of the first organic compound, the second organiccompound, and a simple mixture of the first organic compound and thesecond organic compound.
 2. The organic alloy of claim 1, wherein thedifference between evaporation temperatures of the first organiccompound and the second organic compound is 0° C. to 10° C. at less thanor equal to 10⁻³ torr.
 3. The organic alloy of claim 1, wherein amaximum light emitting wavelength of the organic alloy is shiftedgreater than or equal to 20 nm compared with a maximum light emittingwavelength of a simple mixture of the first organic compound and thesecond organic compound.
 4. The organic alloy of claim 1, wherein theorganic alloy has a color with a longer wavelength region than those ofthe first organic compound, the second organic compound, and the simplemixture of the first organic compound and the second organic compound.5. The organic alloy of claim 1, wherein the organic alloy has adifferent melting point (Tm) than those of the first organic compound,the second organic compound, and the simple mixture of the first organiccompound and the second organic compound.
 6. The organic alloy of claim1, wherein the organic alloy has a constant melting point (Tm).
 7. Theorganic alloy of claim 1, wherein the first organic compound and thesecond organic compound become liquid or vapor at an evaporationtemperature.
 8. The organic alloy of claim 1, wherein the organic alloyis obtained by liquidating or gasifying the first organic compound andthe second organic compound through heat-treatment at greater than orequal to evaporation temperatures thereof and solidifying them throughcooling.
 9. The organic alloy of claim 1, wherein the organic alloy ispresent as a solid or powder at room temperature.
 10. The organic alloyof claim 1, wherein the first organic compound and the second organiccompound are used in a mole ratio of 1:10 to 10:1.
 11. The organic alloyof claim 1, wherein the first organic compound and the second organiccompound are used in a mole ratio of 1:1.
 12. The organic alloy of claim1, wherein the first organic compound has electron characteristics, andthe second organic compound has hole characteristics.
 13. The organicalloy of claim 1, wherein the first organic compound comprises at leastone compound represented by the following Chemical Formula 1, and thesecond organic compound comprises at least one compound represented bythe following Chemical Formula 2:

wherein, in the above Chemical Formula 1, Z is independently N orCR^(a), at least one of Z is N, R¹ to R¹⁰ and R^(a) are independentlyhydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkylgroup, a substituted or unsubstituted C6 to C12 aryl group, or acombination thereof, the total number of 6-membered rings substitutingthe triphenylene group in the Chemical Formula 1 is less than or equalto 6, L is a substituted or unsubstituted phenylene group, a substitutedor unsubstituted biphenylene group or a substituted or unsubstitutedterphenylene group, n1 to n3 are independently 0 or 1, and n1+n2+n3≦1,

wherein, in the above Chemical Formula 2, Y¹ and Y² are independently asingle bond, a substituted or unsubstituted C6 to C30 arylene group, asubstituted or unsubstituted C2 to C30 heterocyclic group, or acombination thereof, Ar¹ and Ar² are independently substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 toC30 heterocyclic group, or a combination thereof, and R¹¹ to R¹³ and R⁴³to R⁴⁴ are independently hydrogen, deuterium, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclicgroup, or a combination thereof.
 14. The organic alloy of claim 13,wherein the first organic compound is represented by the followingChemical Formula 1-I or Chemical Formula 1-II:

wherein, in the above Chemical Formula 1-I or 1-II, Z is independently Nor CR^(a), at least one of Z is N, R¹ to R¹⁰ and R^(a) are independentlyhydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkylgroup, a substituted or unsubstituted C6 to C12 aryl group, or acombination thereof, the total number of 6-membered rings substitutingthe triphenylene group is less than or equal to 6 in the above ChemicalFormula 1-I and Chemical Formula 1-II, L is a substituted orunsubstituted phenylene group, a substituted or unsubstitutedbiphenylene group or a substituted or unsubstituted terphenylene group,n1 to n3 are independently 0 or 1, and n1+n2+n3≧1.
 15. The organic alloyof claim 13, wherein the L of the above Chemical Formula 1 is a singlebond, a substituted or unsubstituted phenylene group having a kinkstructure, a substituted or unsubstituted biphenylene group having akink structure, or a substituted or unsubstituted terphenylene grouphaving a kink structure.
 16. The organic alloy of claim 13, wherein theL of the above Chemical Formula 1 is a single bond or one selected fromsubstituted or unsubstituted groups listed in the following Group 1:

wherein, in the Group 1, R¹⁵ to R⁴² are independently hydrogen,deuterium, a substituted or unsubstituted C1 to C10 alkyl group, asubstituted or unsubstituted C3 to C30 cycloalkyl group, a substitutedor unsubstituted C2 to C30 heterocycloalkyl group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 toC30 heterocyclic group, a substituted or unsubstituted amine group, asubstituted or unsubstituted C6 to C30 arylamine group, a substituted orunsubstituted C6 to C30 heterocyclic amine group, a substituted orunsubstituted C1 to C30 alkoxy group, a halogen, a halogen-containinggroup, a cyano group, a hydroxyl group, an amino group, a nitro group, acarboxyl group, a ferrocenyl group, or a combination thereof.
 17. Theorganic alloy of claim 13, wherein the Ar¹ and Ar² of the above ChemicalFormula 2 are independently substituted or unsubstituted phenyl group, asubstituted or unsubstituted biphenyl group, a substituted orunsubstituted terphenyl group, a substituted or unsubstituted naphthylgroup, a substituted or unsubstituted anthracenyl group, a substitutedor unsubstituted carbazolyl group, a substituted or unsubstitutedbenzofuranyl group, a substituted or unsubstituted benzothiophenylgroup, a substituted or unsubstituted fluorenyl group, a substituted orunsubstituted pyridyl group, a substituted or unsubstituted pyrimidinylgroup, a substituted or unsubstituted pyrazinyl group, a substituted orunsubstituted triazinyl group, a substituted or unsubstitutedtriphenylene group, a substituted or unsubstituted dibenzofuranyl group,a substituted or unsubstituted dibenzothiophenyl group, or a combinationthereof.
 18. The organic alloy of claim 13, wherein the first organiccompound is at least one of compounds listed in the following Group A,and the second organic compound is at least one of compounds listed inthe following Group B:


19. An organic optoelectric device, comprising an anode and a cathodefacing each other, at least one organic layer interposed between theanode and the cathode, wherein the organic layer comprises the organicalloy of claim
 1. 20. A display device comprising the organicoptoelectric device of claim 19.